4-Ethoxymethylphenol: A novel phytoestrogen that acts as an agonist for human estrogen receptors

Virginia Pearce, Zafar Nawaz, Wu Xiao, David Wiedenfeld, Nick Boyle, Don Smith

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

Estrogen is the natural agonist of the estrogen receptor (ER). However, certain plant-derived compounds or phytoestrogens have been identified that mimic estrogens and act as agonists and/or antagonists of ERs, depending on subtype and target tissue. Using thin layer chromatography (TLC), gas chromatography-mass spectrometry (GC-MS), and proton nuclear magnetic resonance (1H-NMR), we identified a simple phenol, 4-ethoxymethylphenol (4EM), found in Maclura pomifera that acts as an agonist of ER-α and ER-β in HeLa and MCF-7 cells. To study the effect of 4EM on ER-α and ER-β activity, we performed transient transfection assays and showed that 4EM activated ER-dependent gene transcription in a dose-dependent manner on both ER subtypes and this activity was inhibited by trans-4-hydroxytamoxifen (4HT). Further, 4EM-mediated transcription in ER-α, like estrogen, was enhanced in the presence of coactivators, steroid receptor coactivator-1 (SRC-1), CREB binding proteins (CBP), and E6-associated protein (E6-AP). We found that 4EM was specific for ER and did not activate transcription of the progesterone receptor.

Original languageEnglish
Pages (from-to)431-439
Number of pages9
JournalJournal of Steroid Biochemistry and Molecular Biology
Volume84
Issue number4
DOIs
StatePublished - Mar 1 2003
Externally publishedYes

Fingerprint

Phytoestrogens
Estrogen Receptors
Estrogens
Transcription
Nuclear magnetic resonance
Maclura
Nuclear Receptor Coactivator 1
CREB-Binding Protein
Thin layer chromatography
MCF-7 Cells
Phytochemicals
Progesterone Receptors
Thin Layer Chromatography
Phenol
4-ethoxymethylphenol
Gas chromatography
Gas Chromatography-Mass Spectrometry
Transfection
Mass spectrometry
Protons

Keywords

  • 4-Ethoxymethylphenol
  • 4HT
  • Agonist
  • CBP
  • Coactivators
  • E6-AP
  • ER-α
  • ER-β
  • Estrogen
  • Estrogen receptor
  • Maclura pomifera
  • Phytoestrogens
  • Progesterone receptor
  • SRC-1
  • Tamoxifen

ASJC Scopus subject areas

  • Biochemistry
  • Endocrinology

Cite this

4-Ethoxymethylphenol : A novel phytoestrogen that acts as an agonist for human estrogen receptors. / Pearce, Virginia; Nawaz, Zafar; Xiao, Wu; Wiedenfeld, David; Boyle, Nick; Smith, Don.

In: Journal of Steroid Biochemistry and Molecular Biology, Vol. 84, No. 4, 01.03.2003, p. 431-439.

Research output: Contribution to journalArticle

Pearce, Virginia ; Nawaz, Zafar ; Xiao, Wu ; Wiedenfeld, David ; Boyle, Nick ; Smith, Don. / 4-Ethoxymethylphenol : A novel phytoestrogen that acts as an agonist for human estrogen receptors. In: Journal of Steroid Biochemistry and Molecular Biology. 2003 ; Vol. 84, No. 4. pp. 431-439.
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